diff --git a/ui/src/pages/model-setup/first-run.test.ts b/ui/src/pages/model-setup/first-run.test.ts
index a162aea214d6..ba5bd9e2d839 100644
--- a/ui/src/pages/model-setup/first-run.test.ts
+++ b/ui/src/pages/model-setup/first-run.test.ts
@@ -164,6 +164,99 @@ describe("model setup first-run redirect", () => {
     ).toEqual(result);
   });
 
+  it("retries one transient detection failure without duplicating either attempt", async () => {
+    const result = {
+      candidates: [],
+      manualProviders: [],
+      workspace: "/tmp/workspace",
+      setupComplete: false,
+    };
+    let rejectFirst!: (error: Error) => void;
+    const request = vi
+      .fn()
+      .mockImplementationOnce(
+        () =>
+          new Promise((_, reject) => {
+            rejectFirst = reject;
+          }),
+      )
+      .mockResolvedValueOnce(result);
+    const client = { request } as unknown as GatewayBrowserClient;
+    type GatewayListener = Parameters<ApplicationContext<RouteId>["gateway"]["subscribe"]>[0];
+    let listener: GatewayListener | null = null;
+    const snapshot = {
+      phase: "connected" as const,
+      client,
+      hello: {
+        auth: { role: "operator", scopes: ["operator.admin"] },
+        features: { methods: ["openclaw.setup.detect"] },
+      },
+    };
+    const replace = vi.fn();
+    const context = {
+      gateway: {
+        snapshot,
+        subscribe: (next: GatewayListener) => {
+          listener = next;
+          return () => undefined;
+        },
+      },
+      agentSelection: {
+        state: { selectedId: "main" },
+        subscribe: () => () => undefined,
+      },
+      replace,
+    } as unknown as ApplicationContext<RouteId>;
+
+    await startRedirect(context);
+    listener!(snapshot as Parameters<GatewayListener>[0]);
+    expect(request).toHaveBeenCalledOnce();
+
+    rejectFirst(new Error("temporary gateway failure"));
+    await vi.waitFor(() => expect(request).toHaveBeenCalledTimes(2));
+    listener!(snapshot as Parameters<GatewayListener>[0]);
+    await vi.waitFor(() => expect(replace).toHaveBeenCalledOnce());
+
+    expect(request).toHaveBeenCalledTimes(2);
+    expect(replace).toHaveBeenCalledWith("model-setup", { search: "?firstRun=1" });
+  });
+
+  it("stops after the same connection rejects detection twice", async () => {
+    const request = vi.fn().mockRejectedValue(new Error("gateway unavailable"));
+    const client = { request } as unknown as GatewayBrowserClient;
+    type GatewayListener = Parameters<ApplicationContext<RouteId>["gateway"]["subscribe"]>[0];
+    let listener: GatewayListener | null = null;
+    const snapshot = {
+      phase: "connected" as const,
+      client,
+      hello: {
+        auth: { role: "operator", scopes: ["operator.admin"] },
+        features: { methods: ["openclaw.setup.detect"] },
+      },
+    };
+    const context = {
+      gateway: {
+        snapshot,
+        subscribe: (next: GatewayListener) => {
+          listener = next;
+          return () => undefined;
+        },
+      },
+      agentSelection: {
+        state: { selectedId: "main" },
+        subscribe: () => () => undefined,
+      },
+      replace: vi.fn(),
+    } as unknown as ApplicationContext<RouteId>;
+
+    await startRedirect(context);
+    await vi.waitFor(() => expect(request).toHaveBeenCalledTimes(2));
+    listener!(snapshot as Parameters<GatewayListener>[0]);
+    await Promise.resolve();
+
+    expect(request).toHaveBeenCalledTimes(2);
+  });
+
   it("does not redirect after the operator leaves the default landing", async () => {
     const result = {
       candidates: [],
diff --git a/ui/src/pages/model-setup/first-run.ts b/ui/src/pages/model-setup/first-run.ts
index 96809e3c3cac..05f8db76a8f1 100644
--- a/ui/src/pages/model-setup/first-run.ts
+++ b/ui/src/pages/model-setup/first-run.ts
@@ -64,8 +64,15 @@ function startModelSetupFirstRunRedirect(params: {
   context: ApplicationContext<RouteId>;
   isStillDefaultLanding: () => boolean;
 }): () => void {
-  let attemptedConnection: ModelSetupDetectionConnection | null = null;
+  let detection:
+    | {
+        connection: ModelSetupDetectionConnection;
+        attempts: number;
+        phase: "in-flight" | "retry-ready" | "settled";
+      }
+    | undefined;
   let redirected = false;
+  let disposed = false;
   const handleSnapshot: Parameters<ApplicationContext<RouteId>["gateway"]["subscribe"]>[0] = (
     snapshot,
   ) => {
@@ -80,16 +87,24 @@ function startModelSetupFirstRunRedirect(params: {
     }
     const agentId = params.context.agentSelection.state.selectedId;
     const connection = { client: snapshot.client, hello: snapshot.hello, agentId };
-    if (
-      connection.client === attemptedConnection?.client &&
-      connection.hello === attemptedConnection?.hello &&
-      connection.agentId === attemptedConnection?.agentId
-    ) {
+    const previous = detection;
+    const sameGeneration =
+      connection.client === previous?.connection.client &&
+      connection.hello === previous?.connection.hello &&
+      connection.agentId === previous?.connection.agentId;
+    if (sameGeneration && previous?.phase !== "retry-ready") {
       return;
     }
-    attemptedConnection = connection;
+    detection =
+      sameGeneration && previous
+        ? { connection, attempts: previous.attempts + 1, phase: "in-flight" }
+        : { connection, attempts: 1, phase: "in-flight" };
+    const attempt = detection;
     void detectModelSetup(snapshot.client, agentId ?? undefined)
       .then((result) => {
+        if (disposed || detection !== attempt) {
+          return;
+        }
         const current = params.context.gateway.snapshot;
         if (
           current.phase !== "connected" ||
@@ -99,6 +114,7 @@ function startModelSetupFirstRunRedirect(params: {
         ) {
           return;
         }
+        detection = { ...attempt, phase: "settled" };
         cacheModelSetupDetection(connection, result);
         if (!result.setupComplete && !redirected && params.isStillDefaultLanding()) {
           redirected = true;
@@ -106,7 +122,15 @@ function startModelSetupFirstRunRedirect(params: {
         }
       })
       .catch(() => {
-        // First-run guidance is best effort. The page offers an explicit retry.
+        if (disposed || detection !== attempt) {
+          return;
+        }
+        // One same-generation retry absorbs a transient startup race without
+        // turning first-run guidance into a background retry loop.
+        detection = { ...attempt, phase: attempt.attempts < 2 ? "retry-ready" : "settled" };
+        if (detection.phase === "retry-ready" && params.isStillDefaultLanding()) {
+          handleSnapshot(params.context.gateway.snapshot);
+        }
       });
   };
   const unsubscribe = params.context.gateway.subscribe(handleSnapshot);
@@ -115,6 +139,7 @@ function startModelSetupFirstRunRedirect(params: {
   );
   handleSnapshot(params.context.gateway.snapshot);
   return () => {
+    disposed = true;
     unsubscribe();
     unsubscribeSelection();
   };